p-Toluenesulfonic acid → Sorafenib Tosylate

HRID 2094794

反応式

HRID 2094794 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[NH:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39]([OH:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1>CC(C)=O>[S:39]([C:36]1[CH:37]=[CH:38][C:33]([CH3:43])=[CH:34][CH:35]=1)([OH:42])(=[O:41])=[O:40].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[NH:10][C:11]2[CH:27]=[CH:26][C:14]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:29]([F:32])([F:30])[F:31]

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 216239Sorafenib

生成物 1

HCID 406563Sorafenib Tosylate収率 94.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpicolinamide (sorafenib base) (100 g, 0.2152 mol) was suspended in acetone (1000 ml) at ambient temperature. p-toluene sulfonic acid (50 g, 0.290 mol) was dissolved in acetone (500 ml) and this solution was charged to above reaction mass drop wise in 15 minutes. The obtained precipitate was stirred for 1-2 hours at ambient temperature, filtered and washed with acetone (500 ml). It was vacuum dried for 12 hours at 50° C. to afford 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpicolinamide tosylate (Sorafenib Tosylate) (130 g).

後処理

  1. additionthis solution was charged to above reaction mass drop wise in 15 minutes
  2. filtrationfiltered
  3. washwashed with acetone (500 ml)
  4. customdried for 12 hours at 50° C.

出典と根拠

ORDレコード
ord-d9c6c366bff14031b2d9871a91e4536a
出典データセット
uspto-grants-2013_05
特許番号
US08445687B2

関連ノート

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